


Two Sides Same Knife

by Waruitenshi



Series: Two Sides Same Knife [1]
Category: Supernatural
Genre: Acceptance, Alternate Universe - Supernatural, Angst and Humor, Angst and Hurt/Comfort, Angst and Romance, Bad Boys' Love, Blood, Blood and Gore, Bloodplay, Bondage, Boys Kissing, Boys' Love, Breaking, Consensual Violence, Corruption, Crossroads Deals & Demons, Dark Dean Winchester, Dark Fantasy, Dean in Hell, Demon Deals, Demon Sex, Demons, Discipline, Disturbing Themes, Dysfunctional Family, Emotional/Psychological Abuse, Enemy Lovers, Falling In Love, Family, Family Issues, Family Secrets, Fluff and Angst, Friendship/Love, Hell, Honesty, Horror, Humor, Imprisonment, Knifeplay, Language, Lima Syndrome, Loss of Innocence, Loss of Virginity, Love/Hate, M/M, Male Slash, Manipulation, Masochism, Master & Servant, Master/Servant, Mind Games, Non-Consensual Violence, One Shot, Other, Pain, Painplay, Porn With Plot, Porn with Feelings, Possessive Alastair, Possessive Behavior, Psychological Horror, Psychological Torture, Psychological Trauma, Sadism, Sexual Content, Sexual Humor, Sexual Violence, Shounen-ai, Slash, Stockholm Syndrome, Suggestive Themes, Suspense, Teacher-Student Relationship, Torture, Twisted, Twisted Romance, Twisted and Fluffy Feelings, Violence, Yaoi, one shot series
Language: English
Status: Completed
Published: 2013-07-01
Updated: 2013-07-01
Packaged: 2017-12-16 18:44:45
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings, Graphic Depictions Of Violence, Major Character Death, No Archive Warnings Apply
Chapters: 1
Words: 9,894
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/865357
Author URL: https://archiveofourown.org/users/Waruitenshi/pseuds/Waruitenshi
Summary: <blockquote class="userstuff">
              <p>Over their time spent in Hell together, Alastair and Dean come to realize that they are simply two sides of the same knife; whether Dean likes it or not. And by the time Alastair is done with him, he just might! Based on Dean being in Hell. Alastair/Dean. Slash/Yaoi. One-Shot. Details Inside.</p>
            </blockquote>





	Two Sides Same Knife

**Author's Note:**

> Yay! First time writing this pairing! It has always fascinated me! X3 Yet another twisted romance I can make and have fun with! Oh what fun!
> 
> Lmfao! I don't know wtf is with me and these two brothers, but I DO so love to torment them so! X3 And it makes it all the more fun because they're such masochists at heart! Kuwahahahahahahahahahah! 
> 
> Also, whenever I picture/write Alastair, I do so as he was in the last meat suit he had. I know he had possessed a human or two before that one but I don't care. LOL! I prefer him this way and I'm gonna say that that is the body he likes to use as it suits him, but since Dean would've recognized him too quickly and there wouldn't have been any fun in that, he switched to a different one under Lilith's orders and keeps the one I prefer him in under a sort of spell and stores the body away like one would do with an expensive suit. 
> 
> And seeing as this is based on Dean's time spent in Hell with Alastair you can bet it's going to be downright demented as some of my other fics if not more so. XD Oh the fun! Oh and when he says "Alas" he's saying it like "Alice". It's a reference joke. And the "Hmn" is Alastair's little laugh like he does in the episode "On the Head of a Pin".
> 
> The way I see it, the demons work with souls the same way they would with a regular human body, except they can do even more since the person will never die from it and they can restart the process as many times as they desire. 
> 
> The title is based off of the phrase: "Two sides, same coin." Because, though they differ, they are very much alike. Well, LoL you get the point (pun intended). XD
> 
> Now! ON WITH THE STORY! Please review! I find them tasty!

He shouted, oh how he shouted! He shouted out for Sam mostly, Bobby too; with the hope that someone would come and save him! Though Dean knew very well that he was now in Hell; strung up agonizingly by meat hooks, it was strangely dark and it seemed as if he were all alone.

The poor boy couldn't tell which was more torturous, the silence that seemed to absorb his screams and made it so that the louder he yelled, the harder they were to hear from his perspective, or that every movement he made caused the hooks to tug and tear at him.

The damned hunter screamed until he became hoarse and the coppery taste of blood bubbled up from where one of the hooks pierced through part of his lung; causing him to cough and cry out in pain, as the convulsing caused more ripping to occur. It was just one of those ironic "damned if you do" situations.

You'd think he'd be smart and cease his fruitless efforts since it was only bound to bring him trouble. But thinking had never really been one of Dean's strong suits to begin with, so the stubborn idiot kept up the repetitious cycle until he felt that he no longer could. And just as he thought such a fate was all Hell had in store for him, a dark figure immerged from the shadows that surrounded him.

"S-Sam…?" He asked meekly; a small spark of hope igniting.

"Not even close _Deano_. Wanna try for the bonus round?" Drawled an eerie, lisping voice from the shady silhouette; snuffing out the spark no sooner than it had formed. Dean had a bad feeling in the pit of his stomach about whoever this was.

He gave an instinctive tug on his painful bindings in an effort to try and go into attack mode, however that only served to remind him that he wasn't going anywhere, and to cause the figure to chortle darkly and come forth.

Dean half expected a demon to step out, which he wasn't technically wrong, its just that the form wasn't what he'd expected. This demon had on a meat suit, or rather was possessing the body of a male human.

The man was tall, slender, and had dark hair; and if he wasn't being puppeteered by an evil monster and Dean wasn't determined to convince himself and everyone else how straight he was, he would've said the guy looked… kinda hot…!

Seeing the other blink in bemusement before unconsciously checking him out with wide doe eyes made the demon chortle again. Interesting reaction he'd just received. Especially considering how it was a hunter _well-known_ for his instant despise of anything he thought to be "evil".

The charcoal suited figure sauntered up to the suffering homo sapien, and as he did, the hooks vanished and Dean was suddenly strung up by his hands, while his legs were tethered to whatever passed for ground here by black chains and shackles; like something from the torture chamber of a dungeon.

Dean's body was now _very_ naked and since he was bound and splayed in front of some demon guy he was awkwardly well aware of it, though he was no longer bloodied or wounded; but he was still sore from it. Too bad for him that at some point the boy would be finding such pain a long reprieve from what was to come…

"Who the hell are you?" The hoarse human demanded angrily.

"Not that it matters, since I'll make quick work of you, _but_ …" The demon paused; regarding the others foolish bravery with faint interest.

"…you can call me Alastair." He added aloofly, while he thought of how he would go about his work with this particularly peculiar specimen.

Alastair was one of the VERY few who _truly_ enjoyed his work, and more than likely the only one who actually preferred being in Hell. He saw what he did as a form of artwork, and here was his new, _lovely_ little canvas just waiting to be painted.

For the eternal life of him, Alastair couldn't quite understand why the higher-ups insisted on regarding this "Dean Winchester" boy as something _so_ special. More than likely he'd just end up a pathetic heap of brutalized flesh and be begging within minutes for it all to stop, just like all the others before him.

Even the masochists who came to the Pit thinking they were going to get their twisted rocks off soon wished they'd never been placed on Alastair's rack. He was just _that good_ at what he did. Hence why he'd earned the title of Master Torturer; certainly not a title earned lightly in such as place as Hell.

A large cart covered with all manner of devilish devices and tools, that Alastair had put together just for his own personal use, appeared beside the demon. Unlike some of the others he didn't bother putting on any kind of smock or gloves, because while those demons disliked the filth that were humans, Alastair far from minded their blood on his hands, or any other part of him for that matter. In fact, he only removed the jacket of the suit he wore and rolled up the sleeves so that he could better _get into_ his work.

He picked up a simple, silvery looking blade. It was one of his favorites because nothing screamed nostalgia or tended to work best than the classics. The simpler tools like this one just helped to make it more… _intimate_. And as anyone knew, he was _quite_ the consummate professional like that.

Dean tried to shy away as the other approached; those piercing blue eyes shining through the eerily dim light before becoming white and causing the man guised demon to look even more intimidating.

But Dean had to be strong. He'd fought all kinds of monsters and been through all manner of obstacles before, so he wasn't about to let some demonic bastard get the best of him so easily!

The smooth, cool metal touched his warm skin and caused an involuntary shiver to run through his body as the white-eyed demon began to ghost it over his torso, like he were tracing out a pattern; but really he just wanted to mess with the bound boy. There was more than one way of torture, and Alastair loved mixing things up.

"You know _Dean_ … I bet you didn't know I had your Daddy dearest down here on my rack." He said idly; every now and then applying a little pressure to the instrument and cutting into the flesh here and there to draw out a sharp hiss. Dean tried to grit his teeth and hold back, but his anger at the mention of his father bubbled up and as usual; his self-control was beginning to waver already.

"Ahhh yes, of course… _family_. Always such an obvious weak spot for most. Whether it was because you loved them too much or had been tormented or traumatized by them somehow; family always comes back to bite you in the ass some way or another. Makes me glad I don't have that problem." Alastair drawled. He could feel the venomous glare and it only made his thin lips twitch into a smirk.

"That's because no one in their right mind would want you as their family. Hell, yours probably killed themselves just to get away from a whacked out creep like you." Dean spat gruffly. Alastair chuckled darkly; beginning to think this Winchester wasn't going to be so dull after all. Not like the last one anyway.

The boys old man didn't even say a word. Not that it wasn't in and of itself impressive by Alastair's standards of course. The man was made of much tougher stuff than most humans seemed to be, but even so, he'd been _quite dull_.

Even after the demon had gone through all the trouble and put up with the uninteresting task of breaking some supposed "important human" (like any of them _could ever_ be special in his eyes), John Winchester never so much as begged for it to end or even looked like he considered the torturers offer of turning the tables and becoming one himself.

Despite his love of his work, the white-eyed demon found it more irksome and tedious than fucking a Dutch Wife, as he'd heard the phrase coined. The man irritated him to no end.

And after all that time he put in trying to break the laughably so-called "righteous man", the son of a bitch ended up getting free when the Devil's Gate opened! A real waste of time in his book. John simply wasn't the right material for the task, even if he HAD broken him. Alastair was good at reading people like that.

 _Ooooh_ , but he could tell Dean was _different_! Something about the lad called to him like a siren to a lost sailor in a storm. And this Winchester was already starting to prove interesting…

"Oh Deano, you cut me to the quick. Too bad I'll be taking my time with mine." He quipped; emphasizing his point by dragging the blade down over where the others ribs lay on the left side of his chest and leaving a long, thin slice from the top rib to the bottom so that it stung like one bitch of a paper cut.

While Alastair eyed the cringing form on his rack, as the boy tried his best to convert all his pain into anger to be all stony like his daddy before him, the demon couldn't help finding it noteworthy how it was only an actual rack if the demon in charge of it wanted it to be. However, he surmised such a coinage was simply easier to convey in conversation rather than calling it by more than one name.

Ah well! Enough digressing, more dissecting! The chief torturer smiled sinisterly as he began to cut and carve away at his tough new hunk of meat; watching with intrigue at just how resistant the hunter was for someone so young.

His father he could get, but this one? He had yet to taste what hellish delights the world had to offer, and here he was all strung up like a bleeding Christmas ornament making nary a sound.

Well, as all good things do, the day came to an end; though it seemed to fly by far too quickly for Alastair's liking, and not fast enough for Dean's. Over and over, and over, and over, and many times over he tore the other down in different ways; before putting him back together like a little kid with a fleshy set of building blocks. And now came the time to make him an offer…

"So Dean my boy, have you had enough yet? Ready to throw in the towel?" The icy eyed demon lisped lazily, as he picked some remnants of the other from his fingernails with a scalpel.

"Screw you douche bag!" Dean spluttered as he spat a mouthful of blood in the others direction. It spattered a little on his shoes, but the crafty creature wasn't the least bit fazed, considering how much gore stained the rest of him at the moment.

"Oooh! Warming up to me _already_ I see. But my offer still stands. Personally I would've taken you for more the swallowing type though. _Pity_ …" He mocked with an amused smirk and a quirking eyebrow.

At this, Dean looked confused. Angry as hell of course as he was trying to hide a LOT of pain, a little disturbed by the others sexual innuendo, but surprised enough that his cheeks were dusted with pink; and still pretty freaking confused.

"What the hell are you talking about?" The hunter asked; trying to ignore the sexual remark and hope the other didn't notice his reaction. Though unfortunately for him, as his shitty luck would have it, Alastair not only saw but found it _noteworthy_. Definitely not a demon you wanted taking any sort of notice of you, but alas! Too little, too late!

"Why, my offer to let you go of course!" He explained as he spread his hands wide in a gesturing motion, as if it were all so obvious and innocent. But Dean wasn't buying it. He narrowed his eyes at the smiling sadist.

"Sounds too good to be true... What's the catch?" Dean really didn't trust this bastard, or any demon or freak that went bump in the night.

"Oh, _good boy_ Deano. Good to know that pumpkin of yours isn't hallowed out after all… well…hmn, perhaps not entirely anyways." The cruel creature mused mockingly, while adroitly and absentmindedly twirling the crimson stained surgical blade in-between his spidery fingers. Dean couldn't help following it with his eyes and feeling a little impressed.

"Well kid, here's the deal. At the end of each and every one of our _sessions_ , I will offer to let you go and put down my blade… _providing_ you pick it up and take it to someone else that is." Alastair elaborated eloquently, but the very offer itself caused such outrage to boil up in the young man that the demon thought the lad might burst! And then, as quickly as the rage began to rumble, it vanished and was replaced with a smug smirk that ol' white eyes was a tad impressed… if only a tad…

"As a matter of fact… why don't you take your damn blade and shove it where the sun don't shine _Alas_ , cuz unlike you, this rabbit ain't trippin' balls on whatever crazy shrooms you got growin' down here." The stubborn man told him derisively as he made fun of his name; only serving to thoroughly entertain the demon.

"And here I thought you'd make this _too_ easy for me… very well then…" Dean watched as the demon grinned wickedly, as he set down the scalpel and picked up a particularly intimidating device that gleamed sinisterly as most of the other demons tools did. Then the other closed back in to elatedly begin their game allllllll over again.

"… Once more down the rabbit-hole then, _shall we_?" Alastair purred fiendishly. He didn't even give the other a chance to retort to that before _burying_ himself in his work again.

And after a good long while of this, the mans resistance showed signs of fracturing, though fine they may be; as he would cry out or scream every once in a while when the tormenter struck a particular nerve or tore at the right spot.

And when Dean did finally let out his first blood curdling shriek, _oooooh_ , what captivating _chills_ it gave the demon! Such a ravishing melody it was to his ears! Blue eyes closed briefly in ecstasy to better help him focus on hearing the pretty music his caged bird would make for him; paying more attention than usual to just what he did to make the other hit such sultry notes so he could _tear_ more out of him.

The days in Hell became weeks, and those turned into months, and even years, with no end in sight for Alastair's seemingly perpetual assault on him (since demons didn't need sleep). And the more time passed, the more the demon enjoyed it!

There was just _something_ about his sessions with Dean Winchester that brought the master torturer to new heights in the satisfaction he got from his art, and enticed him to try even harder than he had with John Winchester to break the boy.

Fourteen years passed in Hell, and that was when Alastair began to realize how _sweet_ and adorable the other could look and sound when he was causing the hunter to writhe and howl in his bindings; which of course were changed depending on what sort of torment he wanted to try out on the other.

It was around seventeen when he found himself fascinated by how the human convulsed and looked when he threw his head back, and his body arched like a perfect U whenever he worked him over _particularly roughly_ ; as if Dean were more in the throes of passion than pain.

And it wasn't very long after that, that Alastair wondered if there was a difference… which made him wonder if perhaps there were a few torture tactics he had _yet_ to try. It was true he tried to stay away from the sexual kind, because he wasn't a whore like his fellow demons were, and had a specific _taste_ when it came to lovers; which had yet to be met… well… so far anyway…

But with Dean, he wanted to see just in what ways he could better bend and break him. To make the arrogant brunette submit to him and finally pick up that knife, so that he could watch as his morbid masterpiece began carving his own. It was shocking to say the least when he found himself growing hard at such tempting contemplations.

Poor, poor Dean had been suffering and bearing through all the hardship as best he could. And though he hated to even think that he might be starting to break down, the hunter continued to endure!

When he was able to, and his vocal cords hadn't began to rebel and his throat rupture; as the cringing taste of blood became more common in his mouth than saliva, the young man would do his best to insult the other and keep up that "screw you" attitude that only one Dean Winchester could.

Though, such efforts were typically met with a smile or something that expressed the demon enjoyed the banter, and of course there were the retorts and quips that would counter the spiteful words and angry one-liners that made it all seem pointless, and that perhaps his efforts would've been better spent keeping his mouth shut.

But in spite of his better judgment, (which wasn't all that great to begin with, let's face it) Dean went on running his mouth anyways… when he wasn't hollering or biting back a scream if he could help it at all. Which was getting steadily harder to do with the way Alastair so cleverly worked.

It was around the nineteenth year when Dean felt his body jerk forward from whatever the heck it was the sick bastard was doing to him, when suddenly he felt long, spidery fingers curl agonizingly in his hair and pull his head down even further; as his crimson smeared lips were crushed against another's that greedily swallowed up his anguish ridden scream.

His eyes shot open wide as he saw just who it was that was kissing him. It was Alastair! And involuntarily his eyes began to flutter closed when the other bit his lip, and before his tired and bemused mind could register it, a gruff groan escaped the hunter. The demon took full advantage of the others parting lips to deepen the osculation.

Alastair didn't realize just how addicting it was to kiss the human until he'd seen how gorgeous the other was a moment ago when he cried out. He wanted to capture that sound to see how it felt, to see if he could _taste_ the utter torment. And when it happened, the demon actually shuddered at how wonderfully warped it was!

Dean tried to struggle and fight the other off; angry at himself because of how much he was starting to enjoy it and hating the bastard for every reason he could think of; especially being such a damn good kisser!

But it didn't take long for his resolve to falter from the way the sadist devoured him so hungrily; like Alastair was a starving man and Dean was his first meal in forever! Which, to be fair, for Alastair, it wasn't too far off lover-wise.

His breath hitched as a silent scream ripped through his brutally abused body when the torturers free hand began working a sharp skinning instrument underneath the flesh of his back.

The sadistic demon bit the others luscious bottom lip hard enough to cut clean through, only for it to begin the slow process of healing so he could do it again later to the boy if he felt like it.

The hunter may have been dead, but in Hell its like your alive but you simply can't die. You're just doomed to live in whatever way they want you to for the rest of your damnation; which was eternity of course.

And Dean wasn't really sure if he'd begun to build up some sort of sick tolerance to all the time spent getting tortured, if insanity was taking hold, or he just hadn't gotten laid in so long, but whatever the reason, despite the ungodly agony, the hunter was finding pleasure in the pain.

As Alastair's hand worked steadily under his skin and his mouth was left wanting when the demon abandoned it to continue his ardent assault on the brunettes neck, Dean's lasciviously twisted, addled mind tried to make himself believe that this was wrong; that he shouldn't find it hot that those spindly fingers under his skin had abandoned the tool to claw and caress him.

That the hot mouth biting and sucking on his neck didn't feel sinfully good and that he hadn't just wantonly pleaded for the other to kiss him again; because he shouldn't have missed the soft feel of facial hair against his clean shaven face, or how damn skilled a kisser the twisted torturer was.

Or that when it all suddenly stopped, he didn't whimper in protest and try to move towards the other despite the tugging and tearing the hooks in his arms and shoulders caused when he did so.

But that evil bastard just gave him a sultry grin; his own blue eyes blazing with lust as he retracted his now bloodied hand from under the flesh, and tantalizingly licked off some of the blood.

Dean watched transfixed and it only encouraged Alastair's desires. It was starting to look like he and the hunter weren't as different as they both thought. Well, more Dean than he, because the demon could sense a similarity in him from the start that was the cause of all this.

 _Now_ if only he could get the human to see and accept it too. Then perhaps he could get him to take up the knife and have the handsome hunter _all_ to himself! So, over the course of the next few months in Hell, Alastair used these new tactics in both the verbal and physical aspects; though there was _plenty_ of psychological to go around too.

Telling Dean how alike they were, and that all he had to do to make it all better was to just accept it and pick up the blade! And the worst part of it, at least in Dean's mind, was that Alastair was using the truth; as much as the hunter tried to deny it.

But he had to take his time. He didn't want to take Dean until he was successful. That way they could celebrate _properly_. But there were a cornucopia of other ways he could defile and violate his darling Deano, so he was happy enough.

"Dean, Dean, _Dean_ …" The Chief Torturer of Hell tsked teasingly while he eyed _his_ defiant little human trying to keep it together. Dean was as usual, a beautiful mess as the demon tended to keep him, and he had yet to break and say that one word that he'd been longing to hear since he first laid icy eyes on the boy.

"Won't you stop pretending we aren't alike and just pick up my knife already?" Alastair asked languidly; holding up the current blade he was using and awaiting the usual answer.

"Why? Have you had enough already?" Was Dean's derisive joke, accompanied by a cocky little smirk that faltered quicker than it usually did. The demon smiled and chuckled; not so much at the others excuse of a joke, but at the spirit he still possessed, well metaphorically speaking, since he was a soul and all.

"Oh quite the contrary! In fact, I'm just getting started. Merely following procedure." Alastair took the blade and ran it down the others spine; making him try and fail to fight back a shudder.

"You know how much of a _stickler_ I am for the rules… don't you?" Alastair replied cheekily. He let the tip of it rest right between the others spread cheeks before impaling the knife all the way inside of Dean as he said "stickler" and paused to hear that _spellbinding_ scream. Only to continue the next bit in a low purr in his prisoners ear, while the poor hunter jerked and failed to fight the sick urge to arch back into it.

"Y-yeah… you're a regular… employee of the month." Dean gritted out acidly, only to shriek again when the metal instrument began twisting ever so slowly inside of him. He wondered how much longer he could endure the whole being tortured thing.

And as it tended to do more frequently that he would admit, Dean had the brief internal argument of maybe it would be easier and better if he just became the torturer instead of remaining the tortured?

It was definitely the more enticing offer, and if he was being honest with himself, which was something he didn't like to do lately, Dean knew that he was better suited to the demons trade.

It was just a natural part of hunting. Sure, he'd usually referred to it as "interrogating" to make it seem less horrible than what others would call or see it, but the brunette knew very well what it was and it had never bothered him before… Especially since he was fairly good at it if his results were enough to go on.

He hated how true Alastair's words were in their likeness. It was like looking into one warped looking-glass, but the image; as distorted as it may be, definitely reflected the truth, and they _both_ knew it.

They were just beginning their thirtieth year in Perdition together, when it happened… Alastair had been going about giving Dean his own unique brand of "special attention", and the hunter had been going through the motions of maddening internal conflict that made him find the torture a nice reprieve; as it allowed him to stop thinking about all of his troubling thoughts and emotions.

And as usual, Alastair would finish up their current session and set down his knife; as he always took to using a blade near the end. He found it the most intimate of all his menacing menagerie. Then, he would speak his offer to Dean.

Since his new brand of tactics, Dean found it took him longer to answer; which made Alastair smirk as he knew the other was starting to understand. Whether he liked it or not. And the white-eyed torturer could tell he was beginning to!

"So Dean… feel like accepting my offer? If you take it off the table, I'll gladly return the favor." Alastair told him in his usual languidly amused and lisping manner. Dean managed to shoot him a glare, but it faltered to a look of uncertainty when the demon loomed closer and leaned in.

Their faces were barely an inch apart and Dean could feel the humid wisps of Alastair's breath tickling against his face like the ends of a spider web. And he couldn't stop himself from trying to lean forward to close the gap; his mind going blank from all his bothersome thoughts and desiring to give in to the bewilderingly blissful touches that the sadist liked to tease him with.

Regardless of if such was probably the worst of all the tortures he'd had to experience; and there had been QUITE a lot, he found he preferred these because at least Dean felt some sort of closeness. It was an utterly ridiculous thing to think or feel, he knew that. But for some reason it just felt… _right_.

Alastair had even somehow found a way to make all of the other tortures he inflicted upon Dean somehow feel more _personal_. Like this was how they were supposed to interact, how they could be closer to each other, and understood the other better than anyone else ever could.

Although, one aspect of their newfound and undefined relationship (though he really had a like/hate feeling about calling it a relationship at all, but he had no other word to describe it) that pissed off Dean the most, was the fact that whenever Alastair started in with the sexual torment, that he would only ever tease the hunter.

He never EVER let Dean reach his climax. Sure, he'd let him get close… _painfully_ close. But never once did the brunette find release. Which, while it disturbed him just how badly he wanted Alastair to give him an orgasm, it was even more so that after each and every time this happened, Dean found it bothered him less and less!

The master torturer smirked at how the other responded and tried to get to him, and so, Alastair closed the gap and curled those skilled fingers into the short, dark brown hair and tightened them painfully as he claimed his hunters mouth in a harsh kiss that Dean returned almost as hungrily; the rich and now familiar mingling flavors of their saliva, Dean's blood, and the oddly intoxicating hint of sulfur that only Alastair (or at least in the brunettes mind) could pull off enthralling them both.

And when Alastair moved back abruptly to further irritate the hunter and let him catch his breath, he couldn't help enjoying the little growl of protest the other managed in his current state.

Though why Dean felt the need to breath was always amusing in itself since it was simply a mind over matter situation. Which was probably the biggest secret of Hell only few demons like himself knew about.

His fingers flexed and tugged sharply on Dean's hair to remind him that he was still waiting for an answer. "Come now Dean. If you just accepted the truth and my offer, you wouldn't have to suffer like this. All you have to do is say " _yes_ " and you can have _anything_ you want." The demon reasoned in a quiet and soft voice so only the brunette could hear. Dean closed his eyes and turned his head away; biting his lip to try and better ignore how soothing he found that damn voice.

He heard an amused laugh and felt those fingers lifting his chin gingerly. "Dean. Look at me Dean." The voice was calm but the demanding undertone caused the young man to begrudgingly open his eyes. Those big green orbs stared into icy blues and the human couldn't help gasping quietly.

"Much better." Alastair smiled; though it was more pleasant than his usual smug one. And Dean blinked in surprise. The white-eyed demon was waiting patiently for the other to answer, but the brunettes brain felt like mush after their rough makeout session.

"Uh…" Was all he could utter; still pretty lost in those startling eyes. "Articulate as always I see." Alastair chortled coolly. Dean frowned, but it ended up looking a bit more like a pout which further entertained the demon.

"Are you going to answer? Or should I simply accept your silence as a "no" and get on with it then?" Alastair's tone was calm but there was something underlying in it that made words spill from Dean's mouth before he could stop himself. "Why, are you bored of me already?" Dean asked in a terse way.

The demons eyes widened; quite taken aback by the hurt in Dean's eyes and voice. Alastair found that _very_ fascinating, and a touch troubling. His blood covered, spidery fingers reached up and traced slowly up and down the others jaw line; smearing the blood and sweat already there with the crimson coating his fingers.

"A little disappointed perhaps… but bored? No. _Never_ with you Dean my boy." Alastair told him coolly and gently. It was the truth, and Dean leaned into the touch and couldn't help finding comfort in that; in spite of the horrific implications of it.

Dean knew that his time in Hell had twisted him. Made him sick like this, that it was all Alastair's fault. Well, maybe partly his own for letting himself feel the things he did. It just didn't feel as great as it originally had to blame everything on the terrifyingly tantalizing torturer.

Now it made his stomach churn like it had when the demon said he felt disappointed in him. Why should he even care? Well, it was hard not to after approximately thirty years of being mutilated and manipulated by the same one who offered the occasional and often just as torturous and ONLY forms of comfort in all of Hell.

Alastair was the only one he'd been around for his entire stay. No other demons came around to torment him like he thought they would. Just the white-eyed torturer. Though, Alastair would once in a blue moon disappear for a short while; which felt like an eternity to Dean, and come back to start their game up again.

He figured maybe it was to give Lilith or whoever a report of his sessions or something. Originally Dean enjoyed the brief breaks from the others presence, but over time, he found he preferred the company to the soul sucking loneliness that came with being imprisoned in the Pit.

But if Dean was really being honest with himself, he _wanted_ to say yes. No one was coming to save him. No one _could_ for that matter. And even if they did, did he really want them to? The answer to that question scared him more than any punishment Alastair could cook up.

What was keeping him from saying no? It's not like eternity would end soon. He had to take care of himself now. No one else was going to do it. Not Sam, or Bobby, or… okay he really didn't have anyone else to count on like that… which was rather depressing. So… apart from pride, which he was pretty sure went out the window when he started taking pleasure in his time with Alastair, what kept him from denying the inevitable…?

"Y-yes…" It was barely a whisper. So quiet that if he hadn't been so close, Alastair wouldn't have noticed the other made a sound. "Hmm? What was that Dean?" The demon asked with a raise of his eyebrow as he eyed him curiously.

"I said… _Yes_." Dean's gruff tone held an air of a perplexing combination of resolve and defeat. Alastair's fingers twitched as he tried to hold back the excitement that began to bubble up at what was happening.

"Yes what?" The demon asked as if he had no idea what the other was talking about. Making Dean give an irate huff and his next words hold more finality and volume. "Yes, I'll pick up the damn knife… Sign me up." He gritted out, only to receive a playful pat on the cheek where the other had previously traced it.

"Ah! So you finally decided to say the magic words! About time Dean. Denial really doesn't suit you." Alastair commented with a smug smirk before snapping his fingers. And as soon as he did, Dean found himself falling limply to his knees; all cleaned up and whole as if he were brand new!

It was much like what happened when Alastair would clean him up to start over in their sessions. Except now he was free of the rack too! At first the hunter didn't move; wondering if the demon was just screwing with him or something.

Then, he heard the other chortle airily and found the courage to get up. Dean never thought he'd appreciate how good it felt to simply be standing on his own two feet, much less move around! He held up his hands to his face and wiggled the fingers experimentally. It had been years since he'd seen his hands…

"As fun as you are to watch Dean, we do have to close your side of the deal for it to be permanent." Alastair informed in his usual drawl. Dean peered at the other between his fingers and then turned to look at the table with the oh too familiar knife as he lowered his hands to his sides.

Alastair casually leaned against the shadows like it was a wall, with his arms crossed loosely over his chest while he watched with interest as the other struggled with that last shred of restraint. "Want to back out? I can understand if you prefer being splayed on my rack. I find it quite the _tantalizing_ image myself." Dean felt his face flush and scowled at the demon who merely smirked, and mentally cursed the sultry sadist for looking so damn fine doing it.

Then, he took a deep breath and after he took his first step, the rest followed easily. And soon he stood before the tray of instruments, with his hand hovering over the handle of Alastair's favorite razor. When Dean picked it up, he knew there was _no_ going back… And so did Alastair.

The instant his fingers curled around the handle, he could feel a shift in the room and heard the frightened whimpering of someone from behind him. Dean whirled around with weapon in hand to see that across from him was a woman tethered to the rack he'd previously been on!

The questioning and somewhat angry look that the other shot him made the chief torturer of Hell laugh icily; causing the hunter to shiver out of something other than fear. "Hmn, hmn. Consider this your own _very special_ version of orientation day Dean." The demon drawled as he approached the other.

He grasped Dean's wrist and lead him over to the rack where the woman's soul gave another whimper as she painfully tried to shrink back. "I picked you out one of the new souls that came in. And don't worry. She deserves _everything_ that's coming to her." Alastair assured him; which again, Dean couldn't help finding comforting on some strange level as he turned the knife unconsciously over in his hand.

However, Dean couldn't bring himself to raise the blade to hurt her. And after a shaky handed attempt at trying to slice into her, the demon realized his appetizing apprentice was going to need some help for his first time. The thought of which made him grin wickedly.

Dean jumped when he felt Alastair come up behind him and place his hand firmly over his own to steady the knife. "No need to be so nervous my boy. This isn't the first person you've sliced into. Just think of her as another demon if you like if it makes this easier for you." The sadist spoke soothingly into the others ear; his breath tickling against the flesh and giving Dean goose pimples.

The demons other hand pulled the brunettes back flat against his chest, before lazily trailing circles over the naked muscular stomach that was tense with anxiety. Dean closed his eyes and tried to bask in what Alastair was doing to him rather than the task at hand. Even though he'd rather not do this at all, it was a far better alternative he decided.

The handsome hunter leaned back into the others warmth and managed to relax a little. A sharp bite to his neck made him yelp and try to jerk away, but the strong hand on his stomach held him in place. "Time to earn your keep Dean." Alastair told him before licking at the blood he drew from the bite.

"And don't worry. I'll be here _every step_ of the way." Dean swallowed hard and this time, as he rose his hand to lay the first incision, it was steadied by Alastair's, and somehow, that strengthened his resolve to know that the other was there like he always was; guiding and supporting him in his own messed up way.

The scream the woman let out when he cut deeply across her collarbone didn't startle or repulse him as much as it probably should have. Instead, it actually did remind him of all the monsters and demon possessed humans he'd cut into, which made the next wound he inflicted easier… as with the ones that followed. And the more he worked her over, the more he was rewarded by Alastair.

" _Goooood_ Dean. Just keep going. Do what feels natural. This is your soul to do with as you please." The demon got a kick out of watching the other work, and decided to make it more fun for both of them as he gave the other little words of encouragement. And Dean ate it up like it was the most delicious slice of pie.

Alastair sucked harshly on the bite mark, and when he did, Dean accidentally dug the blade in deeper than he had originally intended. His deep, gruff groan mixing with the woman's startled cry.

"Oh dear, looks like _someone_ got a little carried away, hmm?" Taunted the demon playfully. And while Alastair made little taunts and teases, the more pain and suffering he inflicted, the better the demon made him feel. Alastair found this form of conditioning coaxed all sorts of delightful reactions from _his_ little hunter.

A well placed bite, lick, kiss, or touch elicited all manner of moans and mewls from Dean. And encouraged the hunter to really get into what he was doing! And it didn't take long before the torturer in training was more hot than bothered.

"Thaaaat's right… use the hooks to hold the flaps of flesh back, that way you can get _right_ in there." His teacher purred instructively. His body felt like it was moving on its own as he lost his focus to what the demon was doing to him and found that now, even with all the pleas for it to stop and everything about this that should've made him sick and ashamed, Dean found that it was no different than cutting into a human who was possessed by a demon.

Not only that, but the hot, slick feeling of blood oozing out over his hands as he filleted the flesh and muscle felt almost as good as it had when the demon had the brunettes trickling down his own body. "Feels good doesn't it? That smooth crimson bit of life dripping down your hands." Alastair slid his hand down the others spine and splayed his hand across the middle as he felt the other leaning into it.

"Like that smooth texture of swallowing a fine wine. The scent just hangs heavy in the air and gives off that enticing little burn that makes you crave _more_ , doesn't it Dean?" He really wasn't in a mind to verbally answer, but Alastair didn't need him to. He could tell everything he needed to by the others body language.

The hunter was so wrapped up in ol' white-eye's words and the soul numbing sensations, that he hardly realized it when Alastair shifted the rack and bent him over it, until the demon torturously began to grind against his firm behind; causing a pleasant jolt to go right to Dean's groin and make him groan and arch back wantonly against the other for more of that wonderful friction.

His mind and body screamed that he needed more though. And after all, Alastair had said he could have anything now that he was cooperating, right? "Alastair…" Dean whispered roughly.

And while Alastair knew what the other wanted; which wasn't hard to tell by the state the boy was in, he still felt like making him say it. "Hmm, yes Dean?" The demon hummed as he nibbled at the others earlobe.

The hunter hated how calm and cool the other sounded. Like they were having a conversation about stamps rather than getting off on some woman's suffering. "Would you just do something already?" He asked in frustration.

"Hmn, like _what_ Deano?" The demon teased; letting his hand brush over the others inner thigh, just avoiding touching the erection he knew was there and making Dean squirm and give a low, rumbling groan.

"Gah! L-like that!" Dean blurted before he could think better of it; his lust getting the better of him as it always had. But for some reason, it was worse when it came to Alastair. "Oh, like this?" Alastair abruptly grasped the hardened flesh; curling those adroit fingers around it like a snake coiling its prey.

Dean gave a breathy gasp and bucked instinctively into the warm hand. "Y-yeah." He gritted out; trying to catch his breath. Trying hard not to keep from breaking entirely. The demon gave a low, dark chuckle that made him quiver and hate that he was completely naked while Alastair was still dressed.

Alastair was delightfully surprised when he felt a tug at his pants and turned his head to see that Dean was trying and failing to push them down with his free hand. He took the prying appendage in his own and put it on the edge of the rack. "If you wanted my pants off, all you have to do is ask Dean." The demon said playfully; licking the shell of the hunters ear and smirking when he heard him give an annoyed growl.

For a long moment, he was sure that Dean wasn't going to say anything to that. But then, the other turned his head just enough and gave the demon a look that might've reduced him to cinders if looks could kill. But being who he was, it only turned him on. "Off. NOW!" Dean demanded through clenched teeth.

If it had been anyone else he'd probably have killed them or said no, but the charming little Winchester was so fun to play with! "How can I say no to that face?" He quipped. And since he'd been waiting VERY patiently to screw Dean into a coma anyway, he smirked and stole a soul searing kiss as he used his powers to get rid of his clothes.

Dean melted into the kiss, as girly as he knew that sounded, but right now, he really didn't give a crap. After around thirty years in Hell, he was FINALLY getting some well deserved attention. So, might as well enjoy it since there was no telling how long it was going to last.

One hand moved with Dean's as he sliced up the woman whose soul healed like all the others, while the other stroked over Dean's length with a ghost light touch that the man found maddening. But no matter how he tried to get more friction it was gleefully denied him.

"Damn it…" He tried to reach his hand down to tend to his problem himself, but his hand was smacked sharply away. "Ah, ah, aaah Deano. None of that. If you want more. Ask me _nicely_." And he could hear the wicked grin in the demons words.

There was a pause as the stubborn Winchester debated whether that was a trick or not. But when the other took his hand off of his aching need entirely, a surprising twinge of panic surged through him. "W-wait!" The hand halted as Alastair waited.

"Fine… _please_?" Dean couldn't believe he'd just asked a demon nicely to jerk him off. Well, he guessed it probably wasn't the weirdest thing that happened to him. Well… maybe… it was a big list and he didn't feel like combing through it right now. Not when all the blood that was supposed to be in his head was rushing someplace lower.

"Good boy." Alastair purred against the neck he was nibbling on; his teeth abusing the already bruised and bleeding flesh. However, instead of feeling the hand back on his groin, he saw the spindly fingers reach out toward the woman in front of him and into one of the gaping gashes.

The demon coated his fingers in the woman's blood before the hand disappeared behind Dean. Something warm and wet pressed between his cheeks as he felt Alastair pushing his legs further apart.

He squirmed a little as he had a pretty good idea what the demon had in mind, but instead of the usual torture device that the demon liked to thrust inside of him, Dean felt two of those long fingers working their way inside of him and a longing moan tore from his throat that surprised both males.

It was still rather uncomfortable, but the blood lubricated it enough that it was far more tolerable than what Dean was used to. And he wondered if that was what made it feel so disturbingly awesome.

They began scissoring him once they were buried inside of him as deep as they could go. The stretching of his tight walls burned and tingled; sending chills up his spine and causing him to arch back against each intrusion.

Alastair was relishing ravishing his handsome hunter; even if it was distracting Dean from torturing. But he supposed if he wasn't holding the brunettes attention, he wasn't doing it right. And that would be such a shame indeed.

The brunette inhaled sharply and his body went ridged as he saw white when those fingers brushed against a certain bundle of nerves inside of him. Alastair made note of this for later and added a third finger.

A few more thrusts against that particular spot and soon he had Dean thrusting back onto his fingers all on his own. He didn't have to do it himself and watched in fascination as the human willingly and wantonly impaled himself on the demons fingers.

"My, aren't we the eager little hunter?" The low, velvety voice mused in his ear. Dean clutched the knife tightly in his hand while he fervently moved back onto the others hand to try and get more of that dementedly delicious friction, while the frightened soul just stared up at him with horribly confused weeping wide eyes.

"Come on my boy, I can feel you just _itching_ to do more to this meatless lump. So go ahead. Nothing left to lose now." For a second the hunter remembered what he was doing and felt bad for the woman's soul.

But then that smooth, sultry voice cascaded over him like it was caressing every molecule of his being and coaxed him into giving in. And so he did, and his need for release overwrought that silly little shred of consciousness as he plunged the sharp blade down into the females stomach!

And just as he did, Alastair switched his fingers for his own throbbing need and impaled Dean in a similar fashion that made it all better. The guilt, the shame and horror of what he would've felt had he been back on the living plane because Sam. Bobby, or his dad told him that was how he was supposed to feel wasn't there anymore.

It was only Alastair to tell him right from wrong. Alastair who consumed him wholly and helped to make him feel good again, and safe and like he was doing what he was meant to. He didn't feel that same disappointment that was present in everyone he'd ever known or as the outcast he knew himself to be.

It was a frightening epiphany to be sure, but once he realized that the true reason he let his old self go and said yes, was because for the first time in all those years since his mother's death, after all the effort he made to keep his family together, it was the demon Alastair who made him feel _home_ … And he didn't want to leave it for anything.

Dean pulled out the bloodied blade and began carving away at the woman's organs with it like a kid with a Halloween pumpkin; the mixed screams of pain that came from the soul and the ones of pleasure coming from Dean mingled into such a beautiful melody Alastair thought.

Seeing the way his boy tore at that damned soul with surprising skill, despite his lust addled mind, brought the demon to new heights of ecstasy he couldn't ever remember experiencing before.

And their sinful symphony continued on like this until Dean couldn't take his aching and ignored manhood being left unattended and did something he never thought he'd do. He pushed himself up enough so that he could stab his length impatiently into the wound he'd made in the side of the souls abdomen and began slamming mercilessly into those hot, slick guts in time with the his demonic lover!

 _Well_ , that was unexpected the demon thought as he felt the judders that wracked his boys body when he'd sheathed himself into the layers of skin and muscle of the side of the females stomach. But he had to give the kid points for originality.

Others; whether newly agreed souls or demons might have wanted to screw an existing hole, but no, his clever Dean went and cut one for himself. Alastair rewarded the other by giving that sensitive spot of nerves a good, hard pounding that caused Dean's mouth to open in a silent scream of rapture as he curved back in an almost spine snapping manner.

With Alastair, every move was precise, controlled, and Dean was slowly learning this as when he tried to get more or speed things up, the other would hold his hips and grip them painfully to tell him no. And so he would have to suffer in a never ending place between pain and pleasure; which is just where the demon wanted him.

The usually heavy air in Hell that was brimming with heat, sulfur, pain and all the other horrors that Alastair thought made it perfect were made all the more so by the freshly spilled blood, sound of flaying flesh and their bodies smacking against each one another.

It was all too much for poor Dean though, and soon the boy came inside his victims guts with a dry, broken scream as his throat had become hoarse from all they had done. The brunettes body spasmed and clenched around the demon. He dug his fingernails into those fine, sinewy hips hard enough to cut and bruise as his rhythm picked up.

The poor soul jerked and gurgled blood like she was having some sort of horrific seizure when his apprentice orgasmed. Though he surmised the fact that he himself was still thrusting mercilessly into his Dean and thus making the exhausted and slumped human rock back and forth wasn't helping matters. Which only served to amuse him as always.

Dean was caught up in his own afterglow and closed his eyes and just let his other senses be engulfed by it all. The feel of those godlike hands on his hips; the tips smoothing over the skin with his own blood before marring it with more marks, the fervent friction as the demon vigorously violated him, and the sexy sounds his hellish lover made.

Though this turned him on the most, as he took a twisted sense of pride in knowing he was the reason why Alastair was making them. And as he managed to open his eyes and glance over his shoulder, he couldn't help shuddering at seeing the demon looming over him so provocatively.

The sight of the chief torturer's lean body glistening with sweat as he watched how his body moved. How he undulated and his muscles flexed with each movement that allowed the demon to thrust deeper into him; filling him up to the point that he felt like Alastair was going to rip him apart. And shivered in the shocking hope that maybe he would.

Alastair looked down to see Dean staring up at him and grinned wickedly; and found it adorable when the other gave a low moan of "Alastair" at his expression. Like his name was a prayer.

Their eyes met and Dean felt like he'd just been shocked with electricity. And before he knew it, he was hard again and moved back to meet the other with a newfound burst of energy. Moaning and gracelessly murmuring the demons name like it was a chant that would save his tainted soul.

They went on like this for what could've been hours or simply minutes. Neither cared to tell, but they both agreed it wasn't long enough. Alastair buried himself as deeply into his hunter as he could when he reached his end. Growling Dean's name in a way that Dean knew to be demonic; as no human could possibly make a sound like that.

Despite that though, the brunette couldn't help liking it and ended up spilling himself for what may have been the third or fourth time into the searing innards of the soul on the rack; whom really wished they'd just leave her alone and go get a damn room.

Alastair rested his body against Dean's. One arm wrapped tightly around his waist and the other curling over his chest with such a fierce possessiveness the human never knew existed.

As Dean closed his eyes and rested his cheek against the warm metal of the rack, he felt the white-eyed demon place sharp yet calm and playful bites and soothing kisses to the area of skin between neck and shoulder.

And with each little bit of brutal affection, Dean's sex addled brain barely registered how greedily the other purred in a low, dark tone "You're _my boy_ now Dean… _Alllll_ _mine_!" But found that instead of filling him with dread, Dean simply smiled and hummed contentedly in agreement.

As the years passed in Hell, Master and Apprentice grew steadily closer and Dean became his favorite and star pupil. Though it wasn't all that surprising, since Alastair was never very far from his hunter. Always there to teach, encourage, and watch, and especially play!

And with Alastair by his side, Dean felt right at home. He tortured souls and offered them that fateful deal the demon had to him not so long ago, and became a sadistic artist in his own right.

However, after about forty years of having been in Hell, there came a day when angels laid siege to the place! Alastair had been off reporting to Lilith as he was supposed to when it happened which was the moment the angels had been waiting for. So by the time word reached him, he was too late to save Dean from those winged pricks!

But he knew he'd have his boy back some day. Hopefully soon, but Alastair had always been a _very_ patient demon. After all, there wasn't much fun in instant gratification as most thought, and the pain of being apart would make their reunion _allllll_ the sweeter!

Because no matter what happened, even if Dean went back to trying to be all goody-goody and was made to believe by those halo wearing chickens that all his wickedness had been washed away, they both knew the truth. That they were and always would be two sides of the same knife…

* * *

**_~The End... of Part One!~_ **

**Author's Note:**

> DUN DUN DUUUUN! Hah! Had yah goin' there for a minute there huh? LOL! Sorry dear reader(s)! Just gotta have some fun! X3
> 
> Anywho! I AM writing a sequel to this, so no worries! Just put me on Author Alert if you wanna know when I put it up on here as I have no exact knowledge of when I'll be done. M'kay? Yay! 
> 
> I DO so love this pairing! Alastair is fun to write! Even more than Crowley and tying with Lucifer! XD
> 
> I like the complex dynamic/relationship between Dean and Alastair. It's even better than Lucifer and Sam in my opinion! And things are gonna be even more fun to mess around with in the next fic though, because I have to deal with Dean trying to change from being who he was in Hell to trying to go back to his old ways for Sam's sake and to save the world and all that blah-biddi-blahness. Lmfao! Get ready for a nice, mental breakdown for Alastair's lil Deano! WOOOOOOOOOH! X3


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